Beilstein J. Org. Chem.2021,17, 932–963, doi:10.3762/bjoc.17.77
’ strategy for the synthesis of zampanolide and dactylolide.
Loh and Chan’s strategy for THP synthesis.
Prins cyclization of cyclohexanecarboxaldehyde.
Prins cyclization of methyl ricinoleate (127) and benzaldehyde (88).
AlCl3-catalyzed cyclization of homoallylic alcohol 129 and aldehyde 130.
Martín and co
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Graphical Abstract
Scheme 1:
General strategy for the synthesis of THPs.
Beilstein J. Org. Chem.2015,11, 1815–1822, doi:10.3762/bjoc.11.197
products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment.
Keywords: Bestmann ylide; dactylolide; dienoate; (triphenylphosphoranylidene)ketene; zampanolide; Introduction
(Triphenylphosphoranylidene)ketene, Ph3P=C=C=O (1), was
structurally related marine natural products, zampanolide (2) and dactylolide (3, Figure 1), wherein the Bestmann ylide represents a C1–C2 linchpin that connects two segments of the macrocylic ring.
(−)-Zampanolide (2, Figure 1) was first isolated from the marine sponge Fasciospongia rimosa found at Cape Zampa
, Japan [21], and subsequently from a Tongan sponge Cacospongia mycofijiensis [22]. It was found to exhibit potent anticancer activities, with IC50 values in the nM scale against a number of cell lines [22][23]. The structurally related compound, (+)-dactylolide, was discovered in the marine sponge
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Graphical Abstract
Figure 1:
Structures of (−)-zampanolide (2) and (+)-dactylolide (3).